What Startups Can Learn from General McChrystal about Combining Strategy and Execution

What Startups Can Learn from General McChrystal about Combining Strategy and Execution

Yammer Co-founder Adam Pisoni speaks with General Stanley McChrystal about the lessons technology companies might take away from his new book Team of Teams.

This article is by Adam Pisoni, co-founder and former CTO of Yammer. He is also a founder of Responsive.org, a new movement dedicated to helping companies become more adaptive and empowering. He recently visited General Stanley McChrystal's consultancy CrossLead to see how he helps companies become more effective.

“No battle plan survives contact with the enemy.” -Helmuth von Moltke

I’ve felt the pain of this quote firsthand. Back when I was running Yammer, I loved strategy meetings. I felt like I was good at hearing everyone’s opinions and encouraging dissent. I also felt like I added a lot of value given how much energy I put into talking to our customers and understanding our market. Yet now, with the benefit of distance, I’m starting to see how those meetings may have failed to drive the successful outcomes we were sure they would. In hindsight, there are a few, interrelated reasons why:

  • Despite having some of the smartest people in the company in these conversations, there was no way this small group had enough context to predict the ramifications of our decisions.
  • Even if we made good strategic decisions, they were never executed by the organization as we naively envisioned. Some of the strategy would be lost or misunderstood as it was communicated through the broader company. A bigger problem though was that each sub-group would interpret the strategy in isolation based on their own goals and constraints. Of course, each team’s implementation would also affect every other team executing the strategy. So even if every group only drifted slightly from the original idea, it would be enough to cause immense confusion and frustration.
  • Since disseminating new strategy decisions was expensive and fraught, we tried not to do it too often. As a consequence, the new strategy was often received with surprise and dismay. Why the “sudden” change? Why weren’t they consulted beforehand? How did we arrive at this? Of course, most people had no way of knowing what we had done or how long it had taken us.

I’ve seen these problems everywhere, at large and small companies alike. So how do you create a cohesive strategy where many people are executing in unison when the strategy and environment are constantly changing?

This is the key lesson in the new book Team of Teams by General Stanley McChrystal, Chris Fussell, Tantum Collins and David Silverman. McChrystal is the former commander of U.S. and International Security Assistance Forces (ISAF) in Afghanistan and the former commander of the nation’s premier military counter-terrorism force, Joint Special Operations Command (JSOC). He was brought into Iraq in 2004 to help turn around the rapidly deteriorating situation there.

After doing so, he left the military to start his own consultancy, CrossLead, which helps companies who face the same problems his forces did in Iraq.

The core problem his forces confronted was that their competitor (a.k.a. Al-Qaeda) was changing the conflict's environment faster than the best military in the world could react and adapt. How could they all stay aligned when the environment and strategy was changing so rapidly — in their case, daily? This is, of course, the same problem almost all companies of any size face.

I recently visited CrossLead to learn more about what they actually did in Iraq and how they help companies do the same.

Depending on your take, McChrystal’s military stories and legacy are either appealing or discomforting. Many of the companies that hire CrossLead do so because they envision former Navy Seals parachuting into their company to whip their employees into shape with strict discipline from the top, as you’d expect from the military.

Imagine their confusion when CrossLead explains their problems aren't about discipline, but lack of trust and common purpose — that they need to develop shared consciousness throughout their organization that will allow them to empower people to make decisions faster on their own. This can't be what they did in Iraq, can it? Well, yes, to a large extent.

The problem in Iraq wasn't that operators were disobedient or didn't work hard enough. The problem was that the chain of command was too slow to move as quickly as the enemy did.

And there were so many things happening in so many places, there was no way for the small group of senior leaders to have enough information to make all the right decisions on their own.

"The wisest decisions are made by those closest to the problem — regardless of their seniority,” General McChrystal says.

His forces came to realize that the only way to move as fast as their enemy was to empower people on the front lines to make decisions as quickly as they could learn new information. But how do you do this when leaders still believe the people on the front lines don’t have enough information to make the right decisions?

This is why trust and common purpose are so critical. Leadership must first trust that employees understand the organization's context and goals enough to make decisions on their own. But how can leadership ever trust their employees if they won't freely share the information people need to make good decisions and let go enough to allow those employees to prove themselves?

McChrystal's answer: By developing shared consciousness. This means getting to a point where you trust almost anyone to make decisions on their own because you believe they have the same information and objectives you do. This is one of the core organizational skills CrossLead helps their customers develop.

While the consultancy employs a number of tactics to help with this, I want to focus on the three I believe to be the most impactful.

Organizational Network Analysis

Companies may have carefully-drawn org charts, but they usually poorly represent the flow of influence and decisions. The real influencers aren’t always the people with the obvious titles. Knowing who these influencers are is key because hierarchies tend to resist change unless the right people see the change as positive.

Even a CEO can't simply dictate a change that requires a new mindset. CrossLead doesn't always like to use military terms, but I'll use one here anyway. One method for changing large social systems is to employ an insurgency strategy. The goal of this is to find key influencers and evangelists and make sure they're involved in the strategy and communication of big changes. Given sufficient critical mass, the rest of the org is likely to follow.

The first thing CrossLead does after being hired is conduct a network analysis of the company. It does this through a series of targeted surveys meant to help expose where the influencers are and how decisions truly get made, regardless of what the org chart might imply.

For example, in many instances, teams will look to other teams for guidance on direction. No matter how much you tell them a new plan is the right course of action, they’ll hesitate until those other teams show excitement as well. Or it’s not uncommon to find teams where the leader of the group is the least liked and influential person among them. Team members may obey their boss to the letter, but may resist in subtle ways until the right people within that team are brought on board.

Once you’ve identified these influencers, you can bring them into the conversation early to make sure they’re supportive of the change you want to make. Without them, it will be difficult.

Battle Rhythms

Part of generating shared consciousness is increasing transparency of projects and process. Creating predictable and frequent rhythms allows large groups to better synchronize their activities. They identify four activities which tend to be done ad hoc and ought to be given regular rhythms:

  • Planning (the future)
  • Deciding (what to do)
  • Monitoring (projects in process)
  • Assessing (what worked and what didn't)

By having inclusive and regular processes for these activities, more people within the organization can come to understand the goals, strategies and learnings. Some examples:

1. At Yammer, projects started and stopped all the time, but on a quarterly basis we’d try to summarize what we had accomplished, what we had learned, and what our focus areas should be for the next quarter.

2. Many companies take a week off every once in a while to gather, reflect and plan. By pulling everyone out of their daily routine at once, they're able to gain better perspective.

3. In Holacracy, every Tactical Meeting starts by going over key metrics important to that group.

4. Every project should end with a post-mortem to talk about whether the goals of the project were met and what was learned as a result. It’s also a time to reflect on what worked or didn’t about the execution itself. Ideally, these findings should be published somewhere everyone can see.

Combining Strategy and Execution

One of McChrystal’s key insights that came from fighting a daily changing war was that separating deciding strategy from disseminating strategy to the troops was simply too difficult and easily messed up. In most organizations, leaders occasionally meet to discuss strategy. These meetings are often infrequent and either instigated by some pressing issue or tied to annual financial rhythms.

At this meeting, leaders might talk about the organization's goals, strategies, resources, competitors, etc. The senior leaders then expect next tier leaders to cascade the relevant parts of what they decide down their ranks. They assume that feedback on the strategy will eventually trickle it's way back up to senior leadership... or not.

Not only is this process too slow, but far too lossy. Given the lengthy game of telephone that usually follows, it's no wonder leaders don't trust their employees to understand strategy. Usually, each leader ends up with their own interpretation which they then further filter based on how much they think their group of employees needs to know. Furthermore, they likely decide which parts are the most important based on their own group’s incentives. As a result, they never get the feedback they need to get better or apply critical information from the front lines.

McChrystal's solution to this problem is to combine the process of talking about strategy with the communication of that strategy to hundreds or thousands of people. While he was active in the military, they did this with a daily, large, inclusive 90-minute strategy meeting with leaders and soldiers from across the various branches of the military as well as people from all the branches of homeland security.

In this well-choreographed meeting, there might be a hundred people in the room and thousands of people listening in on a call. Astoundingly, any of the thousands of people dialed in could speak at any time! McChrystal would be the first to admit it was a long process getting to where this worked at scale, but the end result was a hive mind that ensured everyone was acting with the same information and could be trusted and empowered.

So how does combining strategy and execution work?

1. First, recognize that the goal of these strategy meetings isn’t for leadership to disseminate strategy. That assumes leadership has all the information about what’s going on and what to do, which is usually false. The purpose of the meeting is to develop shared consciousness. It’s to help everyone understand the challenges and priorities of everyone else so the organization can stay aligned even as priorities change. As a desired side effect, people hearing strategic discussions end up not only knowing the strategy, but also how it came to be and who knows what.

2. The goal of this meeting isn’t to solve every problem. That would take too long and potentially end up disempowering people. By helping everyone understand what resources and challenges others have, you're helping people solve their own problems. Much of the role of the leader is to help make connections, clarify who knows or is accountable for what, and encourage people to work together to solve their own problems. It’s also a great forum to recognize the right types of behavior such as cross-collaboration and individual initiative.

3. Having a meeting where there might be 10s, 100s or even 1,000s of people who can speak doesn’t work without clear structure. It will likely take some iteration and a lot of practice. It’s important to have a facilitator who isn’t the most senior leader. Their job is the keep the meeting on task and on schedule. The role of the senior leader is not to pontificate, but to listen and ask questions which would be helpful to everyone else and not just themselves. You’ll probably want to start with a smaller group and expand as you get the hang of it.

4. Here's how this type of meeting might look: 5 minutes of general update. Then each group might get 1-2 minutes to give their quick updates. The goal isn’t to hear what’s happening, but what challenges they are facing and what help they need. Followed by 4 minutes of questions for that group. Again, the goal of the questions isn’t to solve the problem, but to help everyone else understand the issue. This might be followed by seeing if anyone else is having a similar issue or might be able to help. The goal is merely to identify them though, not necessarily solve the issue. Finally, a short 5 minute wrap-up to put everything into context.

5. The meeting’s frequency should match the pace of change in your environment. For most startups, that is probably weekly. For large companies that might be monthly. Any more than that is likely too slow. As a general rule, it should be frequent enough that you don’t feel bad about not getting to everything as the next meeting will come soon enough. Ideally these meetings completely replace private strategy meetings.

Of course, all of the suggestions above are merely tools to move toward distributing authority and empowering people in your organization. If you do not trust your people, are not willing to be transparent, or are uncomfortable sharing power, none of this will likely succeed. Even if you're willing to change, it will likely still be a difficult transition for you.

Most of the examples of leadership we’ve all grown up with teach us the opposite model. We learned that leaders must have the right answer before communicating lest they appear weak or indecisive. We believe that employees simply don’t have enough context to be trusted with the messiness of process. Plus, you want to keep employees focused on their particular area without having to worry about everyone else, right? This might have been right in the past, but it’s increasingly wrong.

If you happen to be working in a stable, predictable environment where there is little new information and change is slow, the old top-down model might still work. The rest of us are just going to have to learn to accept the new pace of reality and realize we can’t do it alone.

Success in unpredictable environments is messy and non-linear. Get over it and bring your employees along for the ride.